Sotolon (YMDB01572)

Identification

YMDB ID

YMDB01572

Name

Sotolon

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

3-Hydroxy-4,5-dimethyl-2(5H)-furanone belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Based on a literature review very few articles have been published on 3-Hydroxy-4,5-dimethyl-2(5H)-furanone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

3-Hydroxy-4,5-dimethyl-2(5H)-furanone
3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon)
3-hydroxy-4,5-dimethyl-5H-furan-2-one
3-hydroxy-4,5-dimethylfuran-2( 5H)-one (sotolon)
3-hydroxy-4,5-dimethylfuran-2(5H)-one
4,5-dimethyl-3-hydroxy-2-(5H)-furanone (sotolon)
4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one (sotolon)
4,5-Dimethyl-3-hydroxy-2(5H)-furanone
Furan-2(5H)-one, 3-hydroxy-4,5-dimethyl-
2,3-Dimethyl-4-hydroxy-2,5-dihydrofuran-5-one
2-Hydroxy-3,4-dimethyl-2-buten-1,4-olide
2-Hydroxy-3-methyl-2-penten-4-olide
3,4-Dimethyl-2-hydroxy-2-butan-1,4-olide
3-Hydroxy-4,5(R)-dimethyl-2(5H)-furanone
3-Hydroxy-4,5-dimethyl-furan-2(5H)-one
4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanone
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
Sautalone
Sotolon
Sotolone

CAS number

28664-35-9

Weight

Average: 128.1259
Monoisotopic: 128.047344122

InChI Key

UNYNVICDCJHOPO-UHFFFAOYSA-N

InChI

InChI=1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3

IUPAC Name

3-hydroxy-4,5-dimethyl-2,5-dihydrofuran-2-one

Traditional IUPAC Name

sotolon

Chemical Formula

C₆H₈O₃

SMILES

CC1OC(=O)C(O)=C1C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butenolide (CHEBI:67890 )

Physical Properties

State

Liquid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	218 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	0.68	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.92 m³·mol⁻¹	ChemAxon
Polarizability	12.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Burnt	FDB003360
Caramel	FDB003360
Celery	FDB003360
Coffee	FDB003360
Cotton candy	FDB003360
Extremely sweet	FDB003360
Fennel	FDB003360
Maple	FDB003360
Seedy	FDB003360
Smoky	FDB003360
Spice	FDB003360
Strong	FDB003360
Sugar	FDB003360
Tobacco	FDB003360

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-7fdd65bce51735b71d12	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05i0-9700000000-43cc2ff6f95044077419	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-9300000000-4d5cfb96c51ba990b353	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zi0-9200000000-3e0b5f2cf3a4e88018fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9000000000-ac732b4b21400d1500e7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3900000000-26b4264da2affe2f394b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-3900000000-eb2c54bf2d77e47495b9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0api-9000000000-1a81a14f56906486c81c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-5900000000-a9b9f4b7467f05d32c85	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aos-9100000000-15b07a7cfd09c718a188	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8bba3e142b490d9cfb12	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-32e912844db31429eab0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9000000000-186c5ec73109434e3baa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-7185ebac9651271eeeee	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Silva Ferreira, A. C., Barbe, J. C., Bertrand, A. (2003). "3-Hydroxy-4,5-dimethyl-2(5H)-furanone: a key odorant of the typical aroma of oxidative aged Port wine." J Agric Food Chem 51:4356-4363.12848510

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB0031306
Pubchem Compound ID	62835
Kegg ID	Not Available
ChemSpider ID	56569
FOODB ID	FDB003360
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xad507884>